Reaction of azetidines with chloroformates |
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Authors: | Vargas-Sanchez Monica Lakhdar Sami Couty François Evano Gwilherm |
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Institution: | Institut Lavoisier de Versailles, UMR CNRS 8180, Université de Versailles Saint Quentin en Yvelines, 45 avenue des Etats-Unis, 78035 Versailles Cedex, France. |
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Abstract: | The reaction of an azetidine with a chloroformate can give either the dealkylated heterocycle or the ring-opened product (gamma-chloroamine), which can further cyclize to the oxazinanone. A general study of this underrated reaction was conducted and revealed that azetidines can undergo smooth nucleophilic ring-opening reactions to highly functionalized gamma-chloroamines in the presence of a variety of alkyl chloroformates under mild reaction conditions. Yields are usually good, and parameters governing this reaction were evaluated. reaction: see text]. |
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